Note: Today’s essay is an excerpt from my upcoming book, How To Turn 39, which is about aging and how we might do it better.

HTT39 is for folks of all ages, not just elder millennials like myself, and is premised on the idea that we can grow older with intention and make this process our own if we choose to, but that doing so requires we think hard about things we would sometimes prefer not to think about (or which we’re encouraged to ignore).

Taking time to mull and consider and self-analyze through this lens can help us navigate these waters, and this book is meant to stoke those sorts of internal conversations.

HTT39 is now available for pre-order (as an ebook pretty much everywhere, as an audiobook a few places, and as a paperback not at all quite yet, because of how the publishing world works for indie authors; I’ll write more about that soon, but in the meantime here’s a list of places where you can pre-order HTT39), and it’ll be released everywhere and in all formats on May 16 (a month after my 39th birthday, which was yesterday).

If you find value in my work and want to support it, buying one of my books is a great way to do that, and pre-ordering helps tell the algorithms that moderate these sales platforms that my books might be worth showing to other people who are unfamiliar with my work.

(Buying the book in any format on May 16 will do the same, but pre-orders help get that algorithm-influencing operation under way, sooner, so when the book goes live, the pumps are already primed).

A huge thanks in advance if you decide to scoop up a copy, and in the meantime, please enjoy this chapter from the book (one of 50), called Accomplishment:

As we grow older and step into new phases of life, our earlier goals and metrics for success may no longer apply, or no longer apply in the same way.

Segueing from an academic career into a job can be tricky, for instance, because the things that made us successful in school won’t directly map onto work-world success.

Similarly, retiring can be disorienting because many of us at least partly define ourselves through the lens of our jobs and careers, and if we no longer shoulder that money-earning burden, who even are we?

No matter how much we have accomplished in work, in our family life, in our hobbies or volunteering or whatever else, the perception of not having done enough—or maybe we should have done things differently?—can amplify this disorientation. 

When we’re younger, this feeling is non-ideal, but it’s not the end of the world because we have plenty of time (perceptually at least) to fill in any gaps that gnaw at us.

The older we get, though, the less time we have left. Every day lived marks another day closer to death, and a little more time behind us than ahead of us.

Though life once felt infinite and we walked the earth as immortals, dawdling away our bottomless chronologies, that sense of near-boredom eventually becomes a bone-deep awareness of our own finitude, alongside a worry that there’s no way we’ll be able to cram everything we’d like to do into the seemingly scarce existence we have left.

This is silly, of course: the average middle-aged person living in the modern world has decades of life left to enjoy. But it doesn’t feel silly, and the changes we experience to our minds and bodies shape a lot of what we do in the latter half of our lives, nudging us toward triage-like decisions rather than calm, intentional investments in the things that really matter to us.

We’re also more capable of achieving some goals in our later years than in our youths because of our accumulated wisdom, knowledge, and experience, and because we’ll likely have access to more resources and will be in a better position to use them appropriately (rather than thoughtlessly throwing everything we’ve got at said goals, youthfully assuming that if our ham-handed efforts fail, we’ll have enough time to bounce back and try again).

There are a few accomplishment-related things I’ve been trying to keep in mind as I grow older.

First is that it’s important to know what we actually want, and to distinguish those wants from mimetic and inherited wants. This means figuring out when a desire is intrinsic and us-centered, and when a want is actually the consequence of other people wanting something, or being told (perhaps in our formative years) that we should want something, and then treating that extrinsic aspiration as if it were our own.

It’s also important to have an accurate sense of what “enough” means in different facets of our lives, because without a ceiling on that concept we may waste some or all of our time, energy, and resources on (for instance) accumulating more money than we need or attaining the pinnacle of professional prestige, when a smaller bank account and lower-level position would have better served our true needs and wants, freeing up our finite resources for other pursuits.

This is important because without that self-defined, self-optimized ceiling, a single aspect of our lives can drain us of the capacity to invest in other aspects, appropriately, and that can flatten us into one-dimensional versions of ourselves. It can also make it less likely we’ll ever step away from that mono-focus until much later in our lives, because self-protective biases like loss aversion will try to dissuade us from cutting our losses (even when it’s prudent to do so), and because we may never take or have the time to step back and ask ourselves whether we’re doing what we want to be doing.

Second is that our sense of what’s vital, what’s pointless, and what’s nice-to-have (but not fundamental to our happiness) all change as we change, so it’s important to check in on these assumptions periodically, lest we continue to perform familiar routines but enjoy fewer meaningful benefits over time, not noticing the diminishment because the rhythms and habits have become so ingrained in our lives and minds.

Third is that it’s helpful to acknowledge and take stock of what we experience as regret, but to remind ourselves that there are often good reasons we didn’t accomplish something, and many times those tradeoffs were worthwhile, even if we may wonder and worry, coveting the greener grass on the other side of the potentiality fence because we experience the downsides of the path we took, daily, but we can only see the desirable upsides, all the stuff we didn’t get, from the path we didn’t take.

Regrets can be useful because the painful pangs they cause can help us reorient ourselves, helping us do more of the things that will fulfill us (rather than less important stuff) in the future. But they’re also often predicated on ill-informed gut-feelings, and we can experience them even after they’re no longer relevant (when we no longer want the things to which they apply). It’s important we take what we can from regrets, then, but that we don’t develop a habit of wallowing in them without productive purpose.

Finally, it’s helpful to incorporate more “atelic” activities (those without defined end-points or concrete goals) into our lives to temper the “telic” ones (those with definitive cut-offs and outcomes) as we grow older.

This helps us become accustomed to doing things just to do them, enjoying the journey and not living exclusively for the destination, and it can help us define ourselves in non-accomplishment-oriented terms.

Many of us find it difficult to do this, especially in a world where our perceived value is largely determined by our economic activity. Incorporating stuff we do for fun, stuff we do while staying in the moment, and stuff that’s just exploratory and experimental (rather than focused on a fixed outcome and end-date), then, can help us chisel new facets into our sense of self, rounding us out while making us less reliant on attainments of a monetizable, socially celebrated, often age-bracketed variety.

If you’d like to pre-order How To Turn 39, you can do so here.

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